Triethylamine → HCID 58542409, compound

HRID 1951915Notes

Reaction equation

HRID 1951915 reaction equation
[C:1]([Si:5]([CH3:8])([CH3:7])Cl)([CH3:4])([CH3:3])[CH3:2].[CH2:9]([N:16]1[C:23](=[O:24])[C:20]2([CH2:22][CH2:21]2)[NH:19][C:18](=[O:25])[CH:17]1[CH2:26][OH:27])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.C(N(CC)CC)C>CN(C)C1C=CN=CC=1.CN(C)C=O>[CH2:9]([N:16]1[C:23](=[O:24])[C:20]2([CH2:21][CH2:22]2)[NH:19][C:18](=[O:25])[CH:17]1[CH2:26][O:27][Si:5]([C:1]([CH3:4])([CH3:3])[CH3:2])([CH3:8])[CH3:7])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 28928tert-Butyldimethylsilyl chlorideHCID 585423617-Benzyl-6-(hydroxymethyl)-4,7-diazaspiro[2.5]octane-5,8-dione

Product 1

HCID 58542409HCID 58542409, compoundYield 85.3%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolvent

Procedure

4-dimethylaminopyridine (660 mg, 5.00 mmol) and tert-butyldimethylchlorosilane (4.90 g, 32.0 mmol) were added to a dimethylformamide (100 ml) solution of the compound (7.15 g, 27.0 mmol) obtained in Step 4 above and triethylamine (4.5 ml, 32.0 mmol). The resulting mixture was stirred at room temperature for 16 hours, then ice water (200 ml) was added to the reaction mixture and the precipitated solid was collected by filtration. The solid obtained was purified by silica gel column chromatography [n-hexane:ethyl acetate=3:1 (v/v)] to give the title compound (8.63 g, 85%) as a colorless solid.

Workup

  1. filtrationthe precipitated solid was collected by filtration
  2. customThe solid obtained
  3. customwas purified by silica gel column chromatography [n-hexane:ethyl acetate=3:1 (v/v)]

Sources & evidence

ORD record
ord-77debab0e8694fddac62fadcab962ea0
Source dataset
uspto-grants-2013_03
Patent number
US08404691B2

Reaction notes

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